Hydrogen Bromide → HCID 14546500, compound

HRID 1789171Notes

Reaction equation

HRID 1789171 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:17]=[CH:16][C:14](N)=[CH:13][CH:12]=2)=[N:6][CH:7]=1.[BrH:18].N([O-])=O.[Na+].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>O.CC(C)=O.CO>[Br:18][CH:24]([CH2:25][C:14]1[CH:16]=[CH:17][C:11]([O:10][CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)=[CH:12][CH:13]=1)[C:23]([O:27][CH3:28])=[O:26]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 13854127HCID 13854127, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14546500HCID 14546500, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 4-[2-(5-methyl-2-pyridyl)ethoxy]aniline (12.0 g), 47% aqueous HBr solution (36.5 g) and methanol (40 ml)-acetone (80 ml) was added dropwise a solution of NaNO2 (4.0 g) in water (10 ml) at 5° C. or below. The whole mixture was stirred at 5° C. for 20 minutes, then methyl acrylate (27.0 g) was added thereto and the temperature was raised to 38° C. Cuprous oxide (1.0 g) was added to the mixture in small portions with vigorous stirring. After nitrogen gas evolution had ceased, the reaction mixture was concentrated under reduced pressure. The concentrate was made alkaline with concentrated aqueous ammonia and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was evaporated off to leave methyl 2-bromo-3-{4-[2-(5-methyl-2-pyridyl)ethoxy]phenyl}-propionate as a crude oil (17.5 g, 87.5%). IR(Neat)cm- 1 : 1735. NMR δ (ppm) in CDCl3 : 2.27 (3H, s), 3.10 (1H, dd, J=14 and 7), 3.22 (2H, t, J=6), 3.38 (1H, dd, J=14 and 7), 3.66 (3H, s), 4.29 (2H, t, J=6), 4.32 (1H, t, J=7), 6.7-7.5 (6H, m), 8.34 (1H, d, J=2).

Workup

  1. temperaturethe temperature was raised to 38° C
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-429220597d424f6884f08146deceabba
Source dataset
uspto-grants-1987_08
Patent number
US04687777

Reaction notes

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